Denis Shapovalov Australian Open

Denis Shapovalov’s best run at the Australian Open came to an end at the hands of one of the best to ever do it.

The 22-year-old Canadian was eliminated at the quarterfinal stage by Rafael Nadal, 6-3, 6-4, 4-6, 3-6, 6-3 in an epic four-hour match.

Shapovalov, who had previously not advanced past the third round at the season’s first major, made things interesting after dropping the first two sets. With the third set on serve at 5-4, Shapovalov converted his first break point of the match to extend things into a fourth. From there, Nadal looked distressed — even calling on a trainer at one point — which allowed Shapovalov to pull even and force a fifth.

However, Nadal composed himself after receiving a medical evaluation between sets and rebounded to win the deciding frame and advance to his 36th Grand Slam semifinal.

Nadal will face the winner of a match later in the day between No. 7 Matteo Berrettini and No. 17 Gael Monfils in the semifinals. If Nadal can go all the way and win the tournament, he would set a new men’s tennis record with his 21st Grand Slam title.